2-Methyl-8-hydroxyquinoline → 2-(Hydroxyiminomethyl)quinolin-8-ol

HRID 1754084

반응식

HRID 1754084 반응식
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([OH:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.OC1C=CC=C2C=1N=C(C=O)C=C2.CC([O-])=O.[Na+].Cl.[NH2:32][OH:33]>O1CCOCC1.O>[OH:12][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([CH:1]=[N:32][OH:33])[CH:11]=[CH:10]2

참가 물질

7

반응물 4

HCID 132242-Methyl-8-hydroxyquinolineHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 5993428-Hydroxy-2-quinolinecarboxaldehyde

생성물 1

HCID 6047332-(Hydroxyiminomethyl)quinolin-8-ol

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매2회

반응 조건

온도
80 °C

실험 절차

A solution of 2-methyl-quinolin-8-ol (536 mg, 3.37 mmol) in dioxane (8 mL) was added dropwise over 3 h into a stirred mixture of SeO2 (665 mg, 5.99 mmol) in dioxane (25 mL) at 50-55° C. The resulting mixture was then heated at 80° C. for 16 h, cooled, and the solids filtered off. The filtrate was concentrated and the residue purified by column chromatography on silica (dichloromethane/MeOH, 1:0-40:1). This afforded 8-hydroxy-quinoline-2-carboxaldehyde 4 as a straw-coloured solid (358 mg, 61%). 4: 1H NMR (CDCl3): δ 10.24 (s, 1 H), 8.34 (d, J=8.6, 1 H), 8.22 (br, 1 H), 8.07 (d, J=8.6, 1 H), 7.64 (dd, J=7.5 and 8.0, 1 H), 7.44 (d, J=8.0, 1 H), 7.30 (d, J=7.5, 1 H). The mixture of 4 (100 mg, 0.578 mmol), NaOAc (63 mg, mmol), hydroxylamine hydrochloride (60 mg, 0.863 mmol) and water (5 mL) was heated at 100° C. for 15 min. The precipitate was isolated by filtration. This provided the title oxime (ID 969) D1 as an off-white solid (87 mg, 80%); spectral data of this compound are shown in Table 2.

후처리

  1. temperaturecooled
  2. filtrationthe solids filtered off
  3. concentrationThe filtrate was concentrated
  4. customthe residue purified by column chromatography on silica (dichloromethane/MeOH, 1:0-40:1)
  5. temperaturewas heated at 100° C. for 15 min
  6. customThe precipitate was isolated by filtration

출처 및 근거

ORD 기록
ord-e2ed331808f4407d965b36dcc4f85dd3
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09169211B2

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